#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007362.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2007362
loop_
_publ_author_name
'Matos Beja, A.'
'Paix\~ao, J. A.'
'Ramos Silva, M.'
'Alte da Veiga, L.'
'Rocha Gonsalves, A. M. D'A.'
'Pinho e Melo, T. M. V. D.'
'Cabral, A. M. T. D. P. V.'
_publ_section_title
;
Methyl
2-(2-Methoxyphenyl)-2,3,3a,4,6,6a-hexahydro-1H-thieno[3,4-b]pyrrole-6a-carboxylate
;
_journal_issue 6
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first 803
_journal_page_last 805
_journal_volume 54
_journal_year 1998
_chemical_formula_moiety 'C15 H19 N O3 S'
_chemical_formula_sum 'C15 H19 N O3 S'
_chemical_formula_weight 293.37
_chemical_name_systematic
;
Methyl
2-(2'-methoxyphenyl)tetrahydro-1H-thieno[3,4-b]pyrrole-6a(6H)-carboxylate
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_audit_creation_method SHELXL97
_cell_angle_alpha 93.036(14)
_cell_angle_beta 102.402(15)
_cell_angle_gamma 98.478(13)
_cell_formula_units_Z 2
_cell_length_a 7.7869(12)
_cell_length_b 9.6947(13)
_cell_length_c 9.849(2)
_cell_measurement_reflns_used 25
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 19.5
_cell_measurement_theta_min 10.4
_cell_volume 715.5(2)
_computing_cell_refinement 'CAD-4 Software'
_computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction 'SDP-Plus (Frenz, 1985)'
_computing_molecular_graphics 'ORTEPII (Johnson, 1976)'
_computing_publication_material SHELXL97
_computing_structure_refinement SHELXL97
_computing_structure_solution 'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'Enraf-Nonius CAD-4'
_diffrn_measurement_method 'profile data from \w-2\q'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71069
_diffrn_reflns_av_R_equivalents 0.012
_diffrn_reflns_av_sigmaI/netI 0.018
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 1
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 3030
_diffrn_reflns_theta_full 25.00
_diffrn_reflns_theta_max 25
_diffrn_reflns_theta_min 3.05
_diffrn_standards_decay_% 1.2
_diffrn_standards_interval_time 300
_diffrn_standards_number 3
_exptl_absorpt_coefficient_mu 0.233
_exptl_absorpt_correction_type none
_exptl_crystal_colour 'translucent yellow'
_exptl_crystal_density_diffrn 1.362
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prismatic
_exptl_crystal_F_000 312
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.38
_exptl_crystal_size_min 0.38
_refine_diff_density_max 0.210
_refine_diff_density_min -0.220
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.027
_refine_ls_hydrogen_treatment
'H atoms treated by a mixture of independent and constrained refinement'
_refine_ls_matrix_type full
_refine_ls_number_parameters 186
_refine_ls_number_reflns 2510
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.027
_refine_ls_R_factor_all 0.046
_refine_ls_R_factor_gt 0.033
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.3614P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref 0.090
_reflns_number_gt 2095
_reflns_number_total 2510
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file na1332.cif
_[local]_cod_data_source_block an361
_cod_database_code 2007362
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
S1 0.30977(7) 0.08145(5) 0.56930(5) 0.04533(16) Uani d . 1 S
O1 0.50412(19) -0.18515(17) 0.94385(16) 0.0576(4) Uani d . 1 O
O2 0.60986(16) -0.05040(15) 0.79524(14) 0.0442(3) Uani d . 1 O
O3 0.16335(17) -0.50119(13) 0.84090(14) 0.0443(3) Uani d . 1 O
N1 0.16113(19) -0.20684(15) 0.80334(15) 0.0303(3) Uani d . 1 N
H1 0.213(3) -0.261(2) 0.853(2) 0.036 Uiso d . 1 H
C1 0.2985(2) -0.12546(17) 0.74476(17) 0.0285(4) Uani d . 1 C
C2 0.0345(2) -0.28977(18) 0.68345(17) 0.0318(4) Uani d . 1 C
H2 -0.0425 -0.2267 0.6372 0.038 Uiso calc R 1 H
C3 0.1489(2) -0.32838(19) 0.58288(19) 0.0378(4) Uani d . 1 C
H3A 0.2067 -0.4074 0.6118 0.045 Uiso calc R 1 H
H3B 0.0778 -0.3506 0.4884 0.045 Uiso calc R 1 H
C4 0.2854(2) -0.19507(18) 0.59365(17) 0.0319(4) Uani d . 1 C
H4 0.4010 -0.2186 0.5851 0.038 Uiso calc R 1 H
C5 0.2249(3) -0.0931(2) 0.48690(19) 0.0417(5) Uani d . 1 C
H5A 0.0958 -0.1071 0.4593 0.050 Uiso calc R 1 H
H5B 0.2713 -0.1078 0.4044 0.050 Uiso calc R 1 H
C6 0.2623(2) 0.02645(18) 0.73129(19) 0.0355(4) Uani d . 1 C
H6A 0.3376 0.0878 0.8091 0.043 Uiso calc R 1 H
H6B 0.1389 0.0307 0.7321 0.043 Uiso calc R 1 H
C7 0.4801(2) -0.12588(18) 0.84011(18) 0.0319(4) Uani d . 1 C
C8 0.7881(2) -0.0415(2) 0.8792(2) 0.0499(5) Uani d . 1 C
H8A 0.8713 0.0108 0.8345 0.075 Uiso calc R 1 H
H8B 0.8162 -0.1341 0.8897 0.075 Uiso calc R 1 H
H8C 0.7954 0.0045 0.9695 0.075 Uiso calc R 1 H
C9 -0.0854(2) -0.41072(18) 0.72294(17) 0.0327(4) Uani d . 1 C
C10 -0.2683(3) -0.4234(2) 0.6774(2) 0.0448(5) Uani d . 1 C
H10 -0.3153 -0.3542 0.6264 0.054 Uiso calc R 1 H
C11 -0.3840(3) -0.5362(3) 0.7053(3) 0.0600(6) Uani d . 1 C
H11 -0.5064 -0.5436 0.6714 0.072 Uiso calc R 1 H
C12 -0.3154(3) -0.6364(2) 0.7833(3) 0.0591(6) Uani d . 1 C
H12 -0.3918 -0.7114 0.8040 0.071 Uiso calc R 1 H
C13 -0.1340(3) -0.6269(2) 0.8313(2) 0.0475(5) Uani d . 1 C
H13 -0.0887 -0.6951 0.8849 0.057 Uiso calc R 1 H
C14 -0.0184(2) -0.51619(18) 0.80005(19) 0.0360(4) Uani d . 1 C
C15 0.2395(3) -0.6097(2) 0.9112(2) 0.0568(6) Uani d . 1 C
H15A 0.3670 -0.5881 0.9285 0.085 Uiso calc R 1 H
H15B 0.1989 -0.6967 0.8542 0.085 Uiso calc R 1 H
H15C 0.2038 -0.6175 0.9983 0.085 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0447(3) 0.0419(3) 0.0498(3) 0.0037(2) 0.0098(2) 0.0214(2)
O1 0.0439(8) 0.0710(10) 0.0509(9) -0.0004(7) -0.0045(7) 0.0328(8)
O2 0.0267(6) 0.0624(9) 0.0417(7) 0.0024(6) 0.0040(5) 0.0176(6)
O3 0.0405(7) 0.0405(7) 0.0543(8) 0.0104(6) 0.0100(6) 0.0174(6)
N1 0.0322(8) 0.0302(8) 0.0278(7) 0.0016(6) 0.0072(6) 0.0039(6)
C1 0.0291(8) 0.0289(8) 0.0277(8) 0.0038(7) 0.0071(7) 0.0049(7)
C2 0.0323(9) 0.0324(9) 0.0294(9) 0.0030(7) 0.0051(7) 0.0048(7)
C3 0.0454(11) 0.0367(10) 0.0295(9) 0.0003(8) 0.0092(8) 0.0005(7)
C4 0.0306(9) 0.0379(9) 0.0276(9) 0.0041(7) 0.0079(7) 0.0037(7)
C5 0.0394(10) 0.0520(12) 0.0313(9) 0.0001(9) 0.0056(8) 0.0130(8)
C6 0.0346(9) 0.0334(9) 0.0402(10) 0.0085(7) 0.0091(8) 0.0079(8)
C7 0.0334(9) 0.0309(9) 0.0303(9) 0.0047(7) 0.0047(7) 0.0037(7)
C8 0.0279(10) 0.0657(14) 0.0520(12) 0.0034(9) 0.0017(9) 0.0096(10)
C9 0.0340(9) 0.0322(9) 0.0303(9) -0.0001(7) 0.0078(7) 0.0005(7)
C10 0.0358(10) 0.0511(12) 0.0443(11) 0.0025(9) 0.0050(8) 0.0064(9)
C11 0.0365(11) 0.0699(15) 0.0657(15) -0.0127(11) 0.0091(10) 0.0026(12)
C12 0.0566(14) 0.0494(13) 0.0662(15) -0.0194(11) 0.0225(12) 0.0009(11)
C13 0.0605(13) 0.0331(10) 0.0490(12) -0.0016(9) 0.0183(10) 0.0065(9)
C14 0.0409(10) 0.0316(9) 0.0352(9) 0.0018(8) 0.0114(8) -0.0004(7)
C15 0.0651(14) 0.0490(12) 0.0636(14) 0.0272(11) 0.0153(12) 0.0180(11)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C6 S1 C5 90.18(8) yes
C7 O2 C8 116.68(14) ?
C14 O3 C15 118.42(15) ?
C1 N1 C2 105.84(13) yes
C1 N1 H1 105.5(14) ?
C2 N1 H1 108.8(14) ?
N1 C1 C7 108.87(13) ?
N1 C1 C6 110.16(13) ?
C7 C1 C6 110.19(14) ?
N1 C1 C4 107.73(13) yes
C7 C1 C4 111.82(14) ?
C6 C1 C4 108.03(13) ?
N1 C2 C9 114.15(14) ?
N1 C2 C3 105.20(13) yes
C9 C2 C3 115.65(15) ?
N1 C2 H2 107.1 ?
C9 C2 H2 107.1 ?
C3 C2 H2 107.1 ?
C4 C3 C2 102.88(14) yes
C4 C3 H3A 111.2 ?
C2 C3 H3A 111.2 ?
C4 C3 H3B 111.2 ?
C2 C3 H3B 111.2 ?
H3A C3 H3B 109.1 ?
C5 C4 C3 113.06(15) yes
C5 C4 C1 108.85(14) ?
C3 C4 C1 103.52(13) yes
C5 C4 H4 110.4 ?
C3 C4 H4 110.4 ?
C1 C4 H4 110.4 ?
C4 C5 S1 107.13(12) yes
C4 C5 H5A 110.3 ?
S1 C5 H5A 110.3 ?
C4 C5 H5B 110.3 ?
S1 C5 H5B 110.3 ?
H5A C5 H5B 108.5 ?
C1 C6 S1 108.33(12) yes
C1 C6 H6A 110.0 ?
S1 C6 H6A 110.0 ?
C1 C6 H6B 110.0 ?
S1 C6 H6B 110.0 ?
H6A C6 H6B 108.4 ?
O1 C7 O2 123.56(16) ?
O1 C7 C1 124.52(16) ?
O2 C7 C1 111.92(14) ?
O2 C8 H8A 109.5 ?
O2 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
O2 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C10 C9 C14 117.67(17) ?
C10 C9 C2 119.86(16) ?
C14 C9 C2 122.41(16) ?
C9 C10 C11 122.1(2) ?
C9 C10 H10 118.9 ?
C11 C10 H10 118.9 ?
C12 C11 C10 119.1(2) ?
C12 C11 H11 120.5 ?
C10 C11 H11 120.5 ?
C11 C12 C13 120.47(19) ?
C11 C12 H12 119.8 ?
C13 C12 H12 119.8 ?
C12 C13 C14 120.3(2) ?
C12 C13 H13 119.8 ?
C14 C13 H13 119.8 ?
O3 C14 C13 123.82(17) ?
O3 C14 C9 115.87(15) ?
C13 C14 C9 120.31(18) ?
O3 C15 H15A 109.5 ?
O3 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O3 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C6 1.803(2) yes
S1 C5 1.803(2) yes
O1 C7 1.192(2) ?
O2 C7 1.327(2) ?
O2 C8 1.443(2) ?
O3 C14 1.369(2) ?
O3 C15 1.422(2) ?
N1 C1 1.471(2) yes
N1 C2 1.476(2) yes
N1 H1 0.82(2) ?
C1 C7 1.521(2) ?
C1 C6 1.547(2) ?
C1 C4 1.578(2) ?
C2 C9 1.510(2) ?
C2 C3 1.534(2) ?
C2 H2 0.9800 ?
C3 C4 1.531(2) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 C5 1.530(2) ?
C4 H4 0.9800 ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C9 C10 1.383(3) ?
C9 C14 1.401(2) ?
C10 C11 1.390(3) ?
C10 H10 0.9300 ?
C11 C12 1.369(3) ?
C11 H11 0.9300 ?
C12 C13 1.378(3) ?
C12 H12 0.9300 ?
C13 C14 1.387(3) ?
C13 H13 0.9300 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O1 0.82(2) 2.24(2) 2.703(2) 115(2)
N1 H1 O3 0.82(2) 2.30(2) 2.899(2) 130(2)
C3 H3A O3 0.97 2.55 3.108(2) 117
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 C7 -138.81(14) ?
C2 N1 C1 C6 100.26(15) ?
C2 N1 C1 C4 -17.36(17) ?
C1 N1 C2 C9 162.94(14) ?
C1 N1 C2 C3 35.11(17) ?
N1 C2 C3 C4 -38.94(17) ?
C9 C2 C3 C4 -165.87(14) ?
C2 C3 C4 C5 -90.61(17) ?
C2 C3 C4 C1 27.00(17) ?
N1 C1 C4 C5 113.77(15) ?
C7 C1 C4 C5 -126.64(15) ?
C6 C1 C4 C5 -5.22(18) ?
N1 C1 C4 C3 -6.75(17) ?
C7 C1 C4 C3 112.84(15) ?
C6 C1 C4 C3 -125.73(15) yes
C3 C4 C5 S1 145.48(13) ?
C1 C4 C5 S1 31.03(16) ?
C6 S1 C5 C4 -38.91(13) ?
N1 C1 C6 S1 -140.25(12) ?
C7 C1 C6 S1 99.61(14) ?
C4 C1 C6 S1 -22.82(16) ?
C5 S1 C6 C1 35.94(13) ?
C8 O2 C7 O1 -0.1(3) ?
C8 O2 C7 C1 179.01(16) ?
N1 C1 C7 O1 1.1(2) ?
C6 C1 C7 O1 122.0(2) yes
C4 C1 C7 O1 -117.9(2) yes
N1 C1 C7 O2 -178.08(14) ?
C6 C1 C7 O2 -57.16(19) ?
C4 C1 C7 O2 63.00(18) ?
N1 C2 C9 C10 125.93(18) ?
C3 C2 C9 C10 -111.79(19) ?
N1 C2 C9 C14 -57.0(2) ?
C3 C2 C9 C14 65.3(2) ?
C14 C9 C10 C11 -0.3(3) ?
C2 C9 C10 C11 176.92(19) ?
C9 C10 C11 C12 1.6(3) ?
C10 C11 C12 C13 -1.2(4) ?
C11 C12 C13 C14 -0.6(3) ?
C15 O3 C14 C13 4.5(3) ?
C15 O3 C14 C9 -175.78(17) ?
C12 C13 C14 O3 -178.34(19) ?
C12 C13 C14 C9 1.9(3) ?
C10 C9 C14 O3 178.77(16) ?
C2 C9 C14 O3 1.6(2) ?
C10 C9 C14 C13 -1.5(3) ?
C2 C9 C14 C13 -178.61(17) ?